Bisamides, Lignans, Triterpenes, and Insecticidal Cyclopenta[<i>b</i>]benzofurans from <i>Aglaia </i>Species

G, Brader; Vajrodaya, Srunya; Greger, Harald; Bacher, Markus; Kalchhauser, Hermann; Hofer, Otmar

doi:10.1021/np9801965

Cited by 104 publications

(139 citation statements)

References 46 publications

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“…2 Flavaglines are a group of compounds representative of the cyclopenta [b] benzofuran-, cyclopenta [b]benzopyran-, and benzo [b]oxepine-type skeletons, all of which are biogenetically derived from flavonoid and cinnamic amide moieties. [2][3][4] To date, about 60 naturally occurring cyclopenta [b]benzofuran-type compounds, many of which exhibit insecticidal and antiproliferative activities, have been isolated from over 30 Aglaia species. The structural variation and biological properties of the flavaglines have been reviewed recently.…”

Section: Introductionmentioning

confidence: 99%

Constituents of the leaves and stem bark of Aglaia foveolata

et al. 2007

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The previously known potent cytotoxic agent silvestrol (1) (0.002% w/w yield) and five new flavagline derivatives (2-6) were isolated from the leaves of Aglaia foveolata collected in Indonesia. The new compound 5 has an unprecedented cyclic amide moiety in its cyclopenta [b]benzopyran skeleton, while compound 6 is a novel benzo [b]oxepine derivative in which the oxepine ring is cleaved. Pyramidatine (7), a biogenetic precursor of the new flavaglines 2-6, was isolated from the leaf extract investigated. Silvestrol was also isolated from the stem bark of A. foveolata (yield of 0.02% w/w) along with a new baccharane-type triterpenoid (8). The structures of the new compounds were elucidated on the basis of their NMR and mass spectrometric data. All new compounds isolated were tested against a panel of cancer cell lines, but only compound 2 was cytotoxic (IC 50 range = 1.4-1.8 μM), and is the first member of the cyclopenta[b]benzopyran class found to exhibit this type of activity. Compound 2 also showed significant NF-κB inhibitory activity in an Elisa assay (IC 50 = 0.37 μM).

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Section: Introductionmentioning

confidence: 99%

Constituents of the leaves and stem bark of Aglaia foveolata

et al. 2007

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“…1 Many 2-arylbenzo[b]furan derivatives are well-known to exhibit broad range of biological activities including anticancer, 2 antiproliferative, 3 anti-inflammatory, 4 antiviral, 5 antifungal, 6 immunosuppressive, 7 antiplatelet, 8 antioxidative, 9 antifeedent, 10 and insecticidal activities. 11 The investigation of structure-activity relationships for 2-arylbenzo[b]furan substituents is still attractive due to variety of biological activities. A number of synthetic approaches to the 2-arylbenzo[b]furan derivatives have been introduced in recent years.…”

Section: Introductionmentioning

confidence: 99%

Facile Preparation of 2-Arylbenzo[b]furan Molecules and Their Anti-inflammatory Effects

Hwang¹,

Jeon²,

Kim³

et al. 2010

Bulletin of the Korean Chemical Society

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An efficient and practical preparation of 2-arylbenzo[b]furan molecules including natural egonol, XH-14, ailanthoidol, and unnatural derivatives is demonstrated using Sonogashira coupling, iodine induced cyclization and Wittig reaction. Anti-inflammatory effects of the prepared benzo[b]furans were examined in lipopolysaccharide (LPS)-stimulated RAW 264-7 macrophages. The results showed that ailanthoidol, XH-14 and three other unnatural derivatives (9-10, 13) inhibited significantly the production of inflammatory mediator nitric oxide without showing cytotoxicity.

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“…Triterpenes are generally considered as main constituents of aglaia, accompanied by significant amounts of sesquiterpenes. Together with typical bisamides, flavaglines represent distinct phytochemical characters restricted to the genus aglaia [3]. Some previously isolated compounds are 29-norcycloart-23-ene-3β,25-diol, 24,25-epoxy-29-norcycloartan-3β-ol, roxburghiadiol-A, dehydroodorine, 2-hydroxyroxburghilin, N-cinnamoyl-2-(2-methylbutanoyl amino) [2].…”

Section: Introductionmentioning

confidence: 99%

“…Some previously isolated compounds are 29-norcycloart-23-ene-3β,25-diol, 24,25-epoxy-29-norcycloartan-3β-ol, roxburghiadiol-A, dehydroodorine, 2-hydroxyroxburghilin, N-cinnamoyl-2-(2-methylbutanoyl amino) [2]. Benzofurans, unique structures of the genus aglaia, were shown to possess high insecticidal properties [3][4][5][6]. High fungicidal activity was also detected against the rice blast disease [7].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Studies on Two Meliaceae plants: Chukrasia Tabularis and Aglaia Roxburghiana

2009

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The paper details a biological investigation on chukrasia tabularis and aglaia roxburghiana, species of meliaceae. The methanol crude extract of chukrasia tabularis and aglaia roxburghiana have been screened for antitumor potentials using brine shrimp lethality bioassay with ten different concentrations. An established cytotoxic agent vincristine sulphate has been used to compare the results. From the graphs the concentration of methanolic crude extract yields the value of LC 50 (50% mortality) as 1.58μg/ml and 2.21μg/ml for chukrasia tabularis and aglaia roxburghiana, respectively. In the same way the concentration at which 90% mortality (LC 90 ) occurs for the methanol extract are obtained from the graphs and the values have been found to be 141.41μg/ml and 70.70μg/ml for chukrasia tabularis and aglaia roxburghiana, respectively.

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Bisamides, Lignans, Triterpenes, and Insecticidal Cyclopenta[b]benzofurans from Aglaia Species

Cited by 104 publications

References 46 publications

Constituents of the leaves and stem bark of Aglaia foveolata

Constituents of the leaves and stem bark of Aglaia foveolata

Facile Preparation of 2-Arylbenzo[b]furan Molecules and Their Anti-inflammatory Effects

Cytotoxic Studies on Two Meliaceae plants: Chukrasia Tabularis and Aglaia Roxburghiana

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